Propargyl alcohol → HCID 9948061, compound

HRID 1069686Notes

Reaction equation

HRID 1069686 reaction equation
[CH2:1]([OH:4])[C:2]#[CH:3].[Na+].[CH3:6][O:7][C:8]1[CH:12]=[CH:11][NH:10][C:9]=1/[CH:13]=[C:14]1\[C:15](=[O:30])[NH:16][C:17]2[C:22]\1=[C:21](C#CCCC([O-])=O)[CH:20]=[CH:19][CH:18]=2>CN(C=O)C.CCN(CC)CC>[OH:4][CH2:1][C:2]#[C:3][C:21]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:22]=1/[C:14](=[CH:13]/[C:9]1[NH:10][CH:11]=[CH:12][C:8]=1[O:7][CH3:6])/[C:15](=[O:30])[NH:16]2

Participants

5

Reactant 2

HCID 7859Propargyl alcoholHCID 23683387HCID 23683387, compound2×

Product 1

HCID 9948061HCID 9948061, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

Using Method D above, propargyl alcohol (43.9 mg, 0.78 mmol) (Aldrich) was coupled with (Z)-4-bromo-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one (100 mg, 0.31 mmol) (Starting Material I supra) using DPPFPdCl2 (12.8 mg) and Cul (3 mg) as catalyst in DMF (3 mL) and Et3N (3 mL) as solvent at 85° C. for 18 h to yield (Z)-1,3-dihydro-4-(3-hydroxy-1-propynyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one. (Yield 42 mg, 46%).

Sources & evidence

ORD record
ord-40214e1c9f294b55b65c30d964b918e8
Source dataset
uspto-grants-2001_06
Patent number
US06252086B1

Reaction notes

Loading…